Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors

被引：44

作者：

Tang, Qidong ^{[1
,3
]}

Wang, Linxiao ^{[1
]}

Tu, Yayi ^{[1
]}

Zhu, Wufu ^{[1
]}

Luo, Rong ^{[2
]}

Tu, Qidong ^{[1
]}

Wang, Ping ^{[1
]}

Wu, Chunjiang ^{[1
]}

Gong, Ping ^{[3
]}

Zheng, Pengwu ^{[1
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Sch Pharm, Nanchang 330013, Peoples R China

[2] Jiangxi Prov Inst Mat Med, Nanchang 330000, Peoples R China

[3] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 07期

关键词：

Synthesis; Pyrrolo[2,3-b]pyridine derivatives; 1,2,3-Triazole; c-Met; Antiproliferative activity; PROSTATE-CANCER; DESIGN; IDENTIFICATION; GROWTH;

D O I：

10.1016/j.bmcl.2016.02.059

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety were designed, synthesized, and evaluated for their c-Met kinase inhibitory activities and antiproliferative activities against 4 cancer cell lines (HT-29, A549, MCF-7, and PC-3) in vitro. Most compounds showed moderate to excellent potency, with the most promising analog 34 showing a c-Met IC50 value of 1.68 nM. Structure-activity relationship studies indicated that electron-withdrawing groups (X = CF3, R-1 = F, R-2 = 4-F) were required to decrease the higher electron density on the 5-atom linker to a proper degree to improve the inhibitory activity. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1680 / 1684

页数：5

共 50 条

[31] Molecular modelling study on pyrrolo[2,3-b]pyridine derivatives as c-Met kinase inhibitors: a combined approach using molecular docking, 3D-QSAR modelling and molecular dynamics simulation
Shirvani, Pouria
Fassihi, Afshin
MOLECULAR SIMULATION, 2020, 46 (16) : 1265 - 1280
[32] Design, synthesis, and biological evaluation of novel substituted benzamide derivatives bearing a 1,2,3-triazole moiety as potent human dihydroorotate dehydrogenase inhibitors
Lu, Kuan
Cai, Lude
Zhang, Xue
Wu, Guodong
Xu, Congjun
Zhao, Yanfang
Gong, Ping
BIOORGANIC CHEMISTRY, 2018, 76 : 528 - 537
[33] 1,2,3-Triazole Derivatives as Novel Antifibrinolytic Drugs
Bosch-Sanz, Oriol
Rabada, Yvette
Biarnes, Xevi
Pedreno, Javier
Caveda, Luis
Balcells, Mercedes
Martorell, Jordi
Sanchez-Garcia, David
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (23)
[34] Synthesis and Evaluation of 1H-Pyrrolo[2,3-b]pyridine Derivatives as Novel Immunomodulators Targeting Janus Kinase 3
Nakajima, Yutaka
Tojo, Takashi
Morita, Masataka
Hatanaka, Keiko
Shirakami, Shohei
Tanaka, Akira
Sasaki, Hiroshi
Nakai, Kazuo
Mukoyoshi, Koichiro
Hamaguchi, Hisao
Takahashi, Fumie
Moritomo, Ayako
Higashi, Yasuyuki
Inoue, Takayuki
CHEMICAL & PHARMACEUTICAL BULLETIN, 2015, 63 (05) : 341 - 353
[35] Synthesis and Antiproliferative Evaluation of Novel Hybrids of Dehydroabietic Acid Bearing 1,2,3-Triazole Moiety
Li, Fang-Yao
Huang, Lin
Li, Qian
Wang, Xiu
Ma, Xian-Li
Jiang, Cai-Na
Zhou, Xiao-Qun
Duan, Wen-Gui
Lei, Fu-Hou
MOLECULES, 2019, 24 (22):
[36] Design and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives bearing an imidazolone moiety as c-Met kinase inhibitors
Liao, Weike
Hu, Gang
Guo, Zhuang
Sun, Deyu
Zhang, Lixia
Bu, Yanxin
Li, Yingxiu
Liu, Yajing
Gong, Ping
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (15) : 4410 - 4422
[37] Synthesis of some pyrrolo[2,3-d]pyrimidine and 1,2,3-triazole isonucleosides
Talekar, RR
Wightman, RH
TETRAHEDRON, 1997, 53 (10) : 3831 - 3842
[38] STUDIES ON 1,2,3-TRIAZOLE DERIVATIVES AS POTENTIAL INHIBITORS OF THE CYCLOOXYGENASE
BIAGI, G
LIVI, O
SCARTONI, V
FARMACO-EDIZIONE SCIENTIFICA, 1987, 42 (04): : 285 - 297
[39] Discovery of novel 2-substituted-4-(2-fluorophenoxy) pyridine derivatives possessing pyrazolone and triazole moieties as dual c-Met/VEGFR-2 receptor tyrosine kinase inhibitors
Gu, Weijie
Dai, Yuxuan
Qiang, Hao
Shi, Wei
Liao, Chen
Zhao, Fangnuo
Huang, Wenlong
Qian, Hai
BIOORGANIC CHEMISTRY, 2017, 72 : 116 - 122
[40] Regioselective one pot synthesis of 1,2,3-triazole derivatives bearing phthalazine moiety and their pharmacological activity
Shyma, P. C.
Kalluraya, Balakrishna
Peethambar, S. K.
Vijesh, A. M.
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (11) : 2680 - 2690

← 1 2 3 4 5 →